Winery Events in Crozet & Western Albemarle

92 Acres

92 Acres is a family-owned and operated distillery, winery, and meadery on the farm just outside Charlottesville where Ragged Branch bourbon was born. After Ragged Branch moved production to Augusta County in 2024, founder Alex Toomy's children Josh Toomy (General Manager & Master Distiller, trained by the late Dave Pickerell) and M. Toomy reimagined the original property as 92 Acres, named for the family farm's acreage. The tasting room at 1015 Taylors Gap Rd. pours 92 Acres' own spirits alongside Ragged Branch bourbons and a seasonal craft cocktail menu, with sweeping Blue Ridge Mountain views. Regular events include Bloody Mary & NFL Sundays, Monday game nights, music bingo, trivia, paint-and-sip classes, and visiting food trucks. Hours: Thu 12–6, Fri–Sat 12–8, Sun 12–6, Mon 4–8. Private events: events@92acres.com.

• Bloody Mary & NFL SundaySun, Oct 25, 2026, 12 PM – 6 PM
• Game NightMon, Oct 26, 2026, 4 PM – 7 PM
• Trivia NightThu, Oct 29, 2026, 6 PM – 8 PM

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Chiswell Farm & Winery

Chiswell Farm & Winery is part of the Chiles Family Orchards, set on a historic Jeffersonian estate in the Virginia countryside in Greenwood, near Crozet on the Monticello Wine Trail. The winery invites guests ages 21 and over to enjoy locally crafted wines, panoramic countryside views, and warm hospitality. Its wines have earned strong recognition, including six awards in the 2026 Virginia Governor's Cup with gold medals for the 2023 Meritage and 2023 Merlot and silver medals for several other vintages. Visitors can build their own tasting flight or choose from recommended flights, including a Governor's Flight of recent award winners, and sip seasonal specialty drinks such as a strawberry citrus spritzer. Open most days of the week, Chiswell also offers the Crown Club membership for those who want to share in the Virginia wine country experience throughout the year.

Outdoor SeatingWeddings

• Witches' Day OutSun, Oct 25, 2026, 1 PM – 4 PM

Fallen Tree Vineyard

Fallen Tree Vineyard is a small-batch farm winery set in the foothills of Crozet, Virginia, within the Monticello AVA. The wines are grown and crafted on site, shaped by the region's hills, weather, and soil, and the portfolio includes Sparkling Rosé, Blanc de Blanc, Chardonnay, Petit Manseng, Viognier, Cabernet Franc, Petit Verdot, and red blends like the Ferenz and Meritage. Visitors can enjoy guided tastings with one-ounce pours led by a wine expert or build a signature flight of four wines with generous two-ounce pours. The on-site kitchen serves wine-friendly small plates featuring local Virginia ingredients, from country ham and artisan cheeses to charcuterie and pizzas, with non-alcoholic options available as well. With sweeping vineyard and mountain views, cozy indoor seating, and outdoor space, Fallen Tree also hosts live music every Saturday and welcomes private events such as weddings and celebrations.

WeddingsOutdoor SeatingFamily Friendly

• Miles Pearce DuoFri, Oct 23, 2026, 4:30 PM – 7:30 PM
• Chelle's Shack Homemade Goods Pop-UpSat, Oct 24, 2026, 1 PM – 4 PM
• The Wavelength TrioSat, Oct 24, 2026, 2:30 PM – 5:30 PM

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Glass House

Glass House Winery is a boutique winery and brewery in central Virginia, founded in 2006 and part of the Monticello Wine Trail near Charlottesville. Known for its tropical flair, the estate grows and cultivates its own grapes to make artisan wines that reflect the terroir of the region, and it has since added the Glass House Brewery to its offerings. Beyond wine and beer, the venue is known for its handcrafted chocolates and its distinctive glass conservatory setting. Weekends often feature live music with local artists, along with special events such as chef-led brunches. Visitors can also extend their stay at the on-site bed and breakfast, making Glass House a destination for a full weekend getaway in Virginia wine country.

DogsOutdoor SeatingOutside Food

• Chickenhead Blues Band with Canelos BurritosFri, Oct 23, 2026, 6 PM – 8:30 PM
• Greg WardSun, Oct 25, 2026, 2 PM – 5 PM
• Dara James and the Soul DisciplesFri, Oct 30, 2026, 6 PM – 8:30 PM

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Grace Estate Winery

Grace Estate Winery is a family-run winery in Crozet, Virginia, about a 15-minute drive from Charlottesville in the Monticello AVA, producing traditionally made, premium artisanal wines from estate-grown old vines in its mountain vineyard. The winery has earned strong critical recognition, including multiple Gold Medals at the Virginia Governor's Cup and high scores from James Suckling for bottlings such as its Slope of Grace Cabernet Franc, Odo Red, Colonel Richard Tannat, and Gange-Rolv Chardonnay. Visitors can reserve tastings and tours, sample current releases in a modern tasting room, and relax on an outdoor patio with a bar, with live music offered every weekend during the season. The historic Grace Estate mansion on the property hosts private events and weddings, and guests can join the Silo Society wine club or shop wines online. With its scenic setting and award-winning lineup, Grace Estate offers a well-rounded Virginia wine country experience.

Weddings

King Family Vineyards

King Family Vineyards is a family-owned and operated winery set in the foothills of the Blue Ridge Mountains in Crozet, Virginia, about 15 minutes from Charlottesville. Farming since 1998, the estate produces premium wines that express the terroir of the Monticello AVA under winemaker Matthieu Finot, including sparkling, white, rosé, and red wines, the Meritage program, and a Small Batch Series. Visitors can taste in the daily-open tasting room, relax on the patio with mountain views, or join Founder's Farm and Vineyard Tours led by co-founder Ellen King aboard a golf cart. A signature draw is Roseland Polo, with Sunday polo matches that invite guests to tailgate and watch from the lawn. The property is also a popular destination for weddings and private events, and offers a wine club for members.

Weddings

• POLOWEEN – Halloween Sunday PoloSun, Oct 25, 2026, 10 AM – 4 PM
• Wine Wednesday – Extended Tasting Room Hours & Food TrucksWed, Oct 28, 2026, 4:30 PM – 8:30 PM
• Balloon GlowSun, Nov 1, 2026, 6 PM – 8:30 PM

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Knights Gambit Vineyard

Knight's Gambit Vineyard is a family-run winery at 218 Knole Farm Lane in Charlottesville, Virginia, where guests come to enjoy estate-grown wines amid vineyard and mountain views. Visitors to the tasting room can sample a flight of all six estate-grown wines, or enjoy their favorites by the glass or bottle. The property features a furnished Cabana Deck, a semi-private micro venue with comfy couches, airy curtains, and seating for up to 20, available to rent for parties, day dates, and family gatherings. The winery also hosts live music and can accommodate weddings and larger private parties. Knight's Gambit is open Thursday through Sunday, with afternoon and evening hours that stretch later toward the weekend.

DogsWeddingsOutdoor Seating

• Sunset Music Series: Ken Farmer & AuthenticatorsSat, Oct 24, 2026, 4 PM – 7 PM
• Sunset Music Series: Buzzard Hollow BoysSat, Oct 31, 2026, 4 PM – 7 PM

Pollak Vineyards

Pollak Vineyards is a small family-owned estate winery in Greenwood, Virginia, set on a farm west of Charlottesville and Crozet against the backdrop of the Blue Ridge Mountains. Founded by the Pollak family in 2003, the winery was built around a simple vision of making estate-grown wines that reflect the beauty and character of the region, with vineyards planted in French vinifera and farmed with a long-term commitment to quality, balance, and a sense of place. The award-winning wines are grown and made on site, and the tasting room and patio offer picturesque views of the vines, the pond, and the nearby mountains. Visitors can enjoy guided wine tastings on weekdays, or stop in any day for glasses, flights, and bottles paired with a la carte cheeses, charcuterie, and fresh bread. The winery is open Wednesday through Monday, and guests can also join the Smuggler Society wine club for preferred pricing and member-only experiences.

Family FriendlyOutdoor Seating

• Final Fridays Concert: Blake Hunter & the GatherersFri, Oct 30, 2026, 5:30 PM – 8:30 PM
• Sip & Savor Express Train RideSat, Nov 7, 2026, 10 AM
• Smuggler SundaySun, Nov 8, 2026, 11 AM

Pro Re Nata Brewpub

Pro Re Nata Brewery is a brewery and music hall in Crozet, Virginia, just west of Charlottesville. Open since 2015, it brews craft beers and pairs them with food, drinks, live music, and a welcoming community atmosphere. The venue is laid out across three distinct zones: the Main Tap Room, home to the kitchen, seating, and a stage with live music most nights; the Original Brewery, featuring a copper bar, guest flags hung from the ceiling, and twelve TVs with full sports packages; and the Farmacy, an open-air event space built around a shipping container with its own outdoor bar, stage, and kids' play area. Outdoor seating surrounds all three areas, with fire pits and scenic views for relaxing. The brewery is open Thursday through Sunday and serves as a popular gathering spot in Central Virginia for any occasion.

Family FriendlyDogsOutdoor Seating

• Big City Band @ Pro Re NataFri, Oct 30, 2026, 7 PM – 10 PM

Septenary Winery

Septenary Winery is a Virginia winery set on historic Seven Oaks Farm, a property whose storied tradition dates back to the 1700s when it was home to one of Virginia's first taverns. The winery is open to the public Thursday through Sunday from 11:00am to 5:30pm, offering wine by the glass or bottle as well as tasting flights. Guests can settle into limited indoor seating or ample outdoor space, with reservations required for groups of six or more and private tastings available by appointment. Septenary is an adults-only facility, welcoming guests 21 and over. Beyond tastings, the winery offers a quarterly wine club and hosts private events and celebrations such as birthdays, anniversaries, rehearsal dinners, and receptions in customizable indoor and outdoor spaces.

Outdoor SeatingPicnic

Starr Hill Brewery - Crozet

Starr Hill Brewery is an independent, regional craft brewery that was born in a Charlottesville music hall in 1999 and has been brewing beer in Virginia ever since. Its Crozet location serves as the brewery's production home and taproom, one of six Starr Hill spots that also include Charlottesville, Lynchburg, Roanoke, Richmond, and Tysons. Visitors to the Crozet taproom can enjoy a rotating lineup of the brewery's craft beers, from year-round favorites to seasonal and limited releases, in a relaxed setting that nods to the brewery's roots in live music. The taproom welcomes guests for casual visits and can also host private events and gatherings. Beyond the beer, Starr Hill offers branded apparel and merchandise, gift cards, and regular news about new brews and label designs.

DogsFamily FriendlyOutdoor Seating

• Trail Run ClubThu, Oct 22, 2026, 6 PM – 7 PM
• Food Truck: PotLucky CvilleTue, Oct 27, 2026, 5:30 PM – 8 PM
• Trivia NightTue, Oct 27, 2026, 7 PM – 9 PM

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Stinson Vineyards

Stinson Vineyards is a family- and winemaker-owned estate winery in Virginia's Blue Ridge Mountains, located near Charlottesville within the Monticello AVA. The winery specializes in small-batch, garagiste-style wines made in small lots, a tradition carried on by the father-daughter team of Scott Stinson and Rachel Stinson Vrooman, who were joined by Rachel's husband Nathan Vrooman in 2015. Visitors can taste the estate's small-production wines in the tasting room while taking in the surrounding mountain views. Guests looking to extend their stay can book a room at The Inn at Stinson Vineyards, the winery's on-site bed and breakfast. The combination of fine wines, scenic setting, and warm hospitality has made it a popular stop in the region's wine country.

B&B

• Session SundaySun, Oct 25, 2026, 1 PM – 4 PM

The Batesville Market

A historic country store in Batesville, operating since 1880 and known over the years as the Charles Joseph Store, Page's Store, the Batesville Store and the Plank Road Exchange. Beer, wine, local food and artisan goods, with a patio and a long-running live music tradition — Charlie Page and Page's Store were the subject of the song "Old Plank Road." Ten minutes south of Crozet and twenty southwest of Charlottesville.

• The PollocksSat, Oct 24, 2026, 7 PM
• Beer & Board GamesTue, Oct 27, 2026, 6:30 PM
• Kai Crowe-Getty Songwriter SpotlightFri, Oct 30, 2026, 7 PM

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